Sulfuric Acid → Benzenesulfonic acid, 3,4-diamino-

HRID 1405327Notes

Reaction equation

HRID 1405327 reaction equation
[C:1]1([NH2:8])[C:2]([NH2:7])=[CH:3][CH:4]=[CH:5][CH:6]=1.[S:9](=O)(=[O:12])([OH:11])[OH:10]>>[NH2:7][C:2]1[CH:3]=[C:4]([S:9]([OH:12])(=[O:11])=[O:10])[CH:5]=[CH:6][C:1]=1[NH2:8]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 7243O-Phenylenediamine

Product 1

HCID 81986Benzenesulfonic acid, 3,4-diamino-

Procedure

To concentrated sulfuric acid (200 mL) at −40° C. was added benzene-1,2-diamine (20 g, 184.95 mmol, 1.00 equiv). The resulting solution was stirred for 30 min at room temperature. Then the resulting solution was stirred overnight at 140° C. in an oil bath. The reaction mixture was cooled to room temperature, quenched by the addition of 500 g of ice, and the solids collected by filtration. The crude product was purified by recrystallization from water, resulting in 9.8 g (28%) of 3,4-diaminobenzenesulfonic acid as a white solid.

Workup

  1. stirringThen the resulting solution was stirred overnight at 140° C. in an oil bath
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customquenched by the addition of 500 g of ice
  4. filtrationthe solids collected by filtration
  5. customThe crude product was purified by recrystallization from water
  6. customresulting in 9.8 g (28%) of 3,4-diaminobenzenesulfonic acid as a white solid

Sources & evidence

ORD record
ord-6ae74b8da9da4b2a90bdcb9291f09000
Source dataset
uspto-grants-2014_12
Patent number
US08916561B2

Reaction notes

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